1. Field of the Invention
This invention pertains to a novel class of 2-amido- or 2-aminoalkyl ethers of polyhydric polyphenols and a method of preparation.
2. Prior Art
The reaction of oxazolines and mono-hydric phenols has been investigated to a limited extent. John A. Frump, Chemical Reviews, Vol. 71, No. 5 (1971) at page 497 states that substituted 2-oxazolines react with phenol in the absence of water to give ethers and carboxamides.
W. Seeliger et al., Agnew. Chem. Internat. Edit., Vol. 5, No. 10 (1966) at page 878, teach that cyclic imidic esters and phenols react most often to produce 2- or 3-substituted N-alkyl amide derivatives, although 2-aminoethyl or 3-aminopropyl esters of carboxylic acids or their derivatives occasionally result.
In German Pat. No. 1,062,253, A. Jager describes the preparation of various ether and carboxamide compounds by treating certain substituted oxazolines with certain phenols, with the exclusion of water. A mixture of phenol and 2-phenyloxazoline refluxed for 7 hours yielded PhCONHCH.sub.2 CH.sub.2 OPh as a product. Similarly, p-bis(oxazolinyl)benzene and phenol gave N,N'-bis(.beta.-phenoxyethyl)terephthalamide. Finally, Jager found that a mixture of 2-phenyl-2-oxazoline and hydroquinone produced 1,4-bis(.beta.-benzamidoethoxy)benzene.
Attempts have also been made to prepare 2-aminoalkyl ethers of phenol by reacting ethylenimine (aziridine) or a C-substituted ethylenimine with phenol. Cf. Dermer and Ham, "Ethylenimine and Other Aziridines" (1969) at page 226. However, such reactions lead to mixed products, mainly polymeric ethylenimine derivatives.
None of the reaction products set forth above contained the polyhydric polyphenol structures of the instant compounds, nor was there any evidence to suggest the high yields common to the instant process. The prior art is void, insofar as we are aware, of any attempts to prepare the amides or amines of polyhydric polyphenols.